Organic Electroluminescent Element And Novel Iridium Complex

ABSTRACT

An iridium complex which has a phenylpyridine bidentate ligand containing a group represented by the following general formula (A): 
     
       
         
         
             
             
         
       
     
     wherein X represents a cyano group or a halogenated alkyl group; L represents a single bond or a divalent linking group; R represents a substituent; n represents an integer of 0 to 4; * represents a binding site to a phenylpyridine bidentate ligand.

TECHNICAL FIELD

The present invention relates to an organic electroluminescent elementand a novel iridium complex. More specifically, the present inventionrelates to an organic electroluminescent element using an iridiumcomplex, in which the iridium complex has three phenylpyridine bidentateligands and at least one phenylpyridine ligand has a phenyl groupsubstituted with a cyano group or a halogenated alkyl group.

BACKGROUND ART

Since organic electroluminescent elements (which may hereinafter also bereferred to as “elements” or “organic EL elements”) are capable ofhigh-luminance light emitting using low voltage driving, they have beenactively researched and developed. The organic electroluminescentelements have organic layers between a pair of electrodes, and utilize,for light emitting, energy of the exciton generated as a result ofrecombination of electrons injected from a cathode and holes injectedfrom an anode in the organic layer.

Recently, by using phosphorescent light emitting materials such as aniridium complex, the efficiency of the elements is increasinglyincreased (see PTLs 1 to 4).

However, elements using iridium complexes in the related art need to befurther improved from the viewpoint of durability.

CITATION LIST Patent Literature

[PTL 1] WO09/073245

[PTL 2] WO09/146770

[PTL 3] JP-A-2001-357977

[PTL 4] JP-A-2006-86482

SUMMARY OF INVENTION Technical Problem

It is an object of the present invention to provide an organicelectroluminescent element having a low driving voltage, excellentefficiency, and excellent durability, and an iridium complex used forfabrication of the element.

Further, it is another object of the present invention to provide acompound useful for the organic electroluminescent elements as describedabove. Further, it is still another object of the present invention toprovide a light emitting device, a display device, and an illuminationdevice, each including the organic electroluminescent element of thepresent invention.

Solution to Problem

The present inventors have investigated and as a result, they have foundthat by introducing a phenyl group substituted with a cyano group or ahalogenated alkyl group into an iridium complex containing threebidentate ligands having phenylpyridine skeletons, the durability of theorganic electroluminescent element is improved significantly.

The present invention can be achieved by the following means.

[1] An organic electroluminescent element including a substrate, a pairof electrodes including an anode and a cathode, disposed on thesubstrate, and at least one organic layer including a light emittinglayer, disposed between the electrodes,

in which at least one kind of compound represented by the followinggeneral formula (1) is contained in at least one of the organic layers.

In the general formula (1), R₁₁₁ to R₁₃₄ each independently represent ahydrogen atom or a substituent. At least two adjacent groups out of R₁₁₁to R₁₁₄, R₁₁₄ and R₁₁₅, at least two adjacent groups out of R₁₁₅ toR₁₁₈, at least two adjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃,at least two adjacent groups out of R₁₂₃ to R₁₂₆, at least two adjacentgroups out of R₁₂₇ to R₁₃₀, R₁₃₀ and R₁₃₁, or at least two adjacentgroups out of R₁₃₁ to R₁₃₄ may be bonded to each other to form a ring,provided that at least one of R₁₁₁ to R₁₃₄ represents a grouprepresented by the following general formula (A).

In the general formula (A), X represents a cyano group or a halogenatedalkyl group. L represents a single bond or a divalent linking group. Rrepresents a substituent. In the case where a plurality of R's arepresent, they may be the same as or different from each other. nrepresents an integer of 0 to 4. * represents a binding site.

[2]

The organic electroluminescent element as described in [1], in which thecompound represented by the general formula (1) is a compoundrepresented by the following general formula (2).

In the general formula (2), R₁₁₁ to R₁₂₃, R₁₂₅, R₁₂₆, and R₂₁₁ to R₂₁₅each independently represent a hydrogen atom or a substituent. Twogroups out of R₁₁₁ to R₁₁₈ may be the same as or different from eachother. At least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅,at least two adjacent groups out of R₁₁₅ to R₁₁₈, at least two adjacentgroups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, R₁₂₅ and R₁₂₆, or at leasttwo adjacent groups out of R₂₁₁ to R₂₁₅ may be bonded to each other toform a ring. L represents a single bond or a divalent linking group,provided that at least one of R₂₁₁ to R₂₁₅ represents a cyano group or ahalogenated alkyl group.

[3]

The organic electroluminescent element as described in [1], in which thecompound represented by the general formula (1) is a compoundrepresented by the following general formula (3).

In the general formula (3), R₁₁₁ to R₁₁₅, R₁₁₇, R₁₁₈, R₁₁₉ to R₁₂₆, andR₃₁₁ to R₃₁₅ each independently represent a hydrogen atom or asubstituent. Two groups out of R₁₁₁ to R₁₁₅, R₁₁₇, R₁₁₈, and R₃₁₁ toR₃₁₅ may be the same as or different from each other. At least twoadjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, R₁₁₇ and R₁₁₈, atleast two adjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, at leasttwo adjacent groups out of R₁₂₃ to R₁₂₆, or at least two adjacent groupsout of R₃₁₁ to R₃₁₅ may be bonded to each other to form a ring. Lrepresents a single bond or a divalent linking group, provided that atleast one of R₃₁₁ to R₃₁₅ represents a cyano group or a halogenatedalkyl group.

[4]

The organic electroluminescent element as described in [1], in which thecompound represented by the general formula (1) is a compoundrepresented by the following general formula (4).

In the general formula (4), R₁₁₁ to R₁₂₀, R₁₂₂ to R₁₂₆, and R₄₁₁ to R₄₁₅each independently represent a hydrogen atom or a substituent. Twogroups out of R₁₁₁ to R₁₁₈ may be the same as or different from eachother. At least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅,at least two adjacent groups out of R₁₁₅ to R₁₁₈, R₁₁₉ and R₁₂₀, R₁₂₂and R₁₂₃, at least two adjacent groups out of R₁₂₃ to R₁₂₆, or at leasttwo adjacent groups out of R₄₁₁ to R₄₁₅ may be bonded to each other toform a ring. L represents a single bond or a divalent linking group,provided that at least one of R₄₁₁ to R₄₁₅ represents a cyano group or ahalogenated alkyl group.

[5]

The organic electroluminescent element as described in [1], in which thecompound represented by the general formula (1) is a compoundrepresented by the following general formula (5).

In the general formula (5), R₁₁₁, R₁₁₂, R₁₁₄, R₁₁₅ to R₁₂₆, and R₅₁₁ toR₅₁₅ each independently represent a hydrogen atom or a substituent. Twogroups out of R₁₁₁, R₁₁₂, R₁₁₄, R₁₁₅ to R₁₁₈, and R₅₁₁ to R₅₁₅ may beeach the same as or different from each other. R₁₁₁ and R₁₁₂, R₁₁₄ andR₁₁₅, at least two adjacent groups out of R₁₁₅ to R₁₁₈, at least twoadjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, at least twoadjacent groups out of R₁₂₃ to R₁₂₆, or at least two adjacent groups outof R₅₁₁ to R₅₁₅ may be bonded to each other to form a ring. L representsa single bond or a divalent linking group, provided that at least one ofR₅₁₁ to R₅₁₅ represents a cyano group or a halogenated alkyl group.

[6]

The organic electroluminescent element as described in [1], in which thecompound represented by the general formula (1) is a compoundrepresented by the following general formula (6).

In the general formula (6), R₁₁₁ to R₁₂₄, R₁₂₆, and R₆₁₁ to R₆₁₅ eachindependently represent a hydrogen atom or a substituent. Two groups outof R₁₁₁ to R₁₁₈ may be each the same as or different from each other. Atleast two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, at leasttwo adjacent groups out of R₁₁₅ to R₁₁₈, at least two adjacent groupsout of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, R₁₂₃ and R₁₂₄, or at least twoadjacent groups out of R₆₁₁ to R₆₁₅ may be bonded to each other to forma ring. L represents a single bond or a divalent linking group, providedthat at least one of R₆₁₁ to R₆₁₅ represents a cyano group or ahalogenated alkyl group.

[7]

The organic electroluminescent element as described in any one of [1] to[6], in which X in the general formula (A), at least one of R₂₁₁ to R₂₁₅in the general formula (2), at least one of R₃₁₁ to R₃₁₅ in the generalformula (3), at least one of R₄₁₁ to R₄₁₅ in the general formula (4), atleast one of R₅₁₁ to R₅₁₅ in the general formula (5), and at least oneof R₆₁₁ to R₆₁₅ in the general formula (6) are cyano groups.

[8]

The organic electroluminescent element as described in any one of [1] to[7], in which a compound represented by any one of the general formulae(1) to (6) is contained in the light emitting layer.

[9]

The organic electroluminescent element as described in [8], furthercontaining a compound having a cyano group, in addition to the compoundrepresented by any one of the general formulae (1) to (6), in the lightemitting layer.

[10] A light emitting device using the organic electroluminescentelement as described in any one of [1] to [9].

[11] A display device using the organic electroluminescent element asdescribed in any one of [1] to [9].

[12] An illumination device using the organic electroluminescent elementas described in any one of [1] to [9].

[13]

A compound represented by the following general formula (2).

In the general formula (2), R₁₁₁ to R₁₂₃, R₁₂₅, R₁₂₆, and R₂₁₁ to R₂₁₅each independently represent a hydrogen atom or a substituent. Twogroups out of R₁₁₁ to R₁₁₈ may be each the same as or different fromeach other. At least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ andR₁₁₅, at least two adjacent groups out of R₁₁₅ to R₁₁₈, at least twoadjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, R₁₂₅ and R₁₂₆, or atleast two adjacent groups out of R₂₁₁ to R₂₁₅ may be bonded to eachother to form a ring. L represents a single bond or a divalent linkinggroup, provided that at least one of R₂₁₁ to R₂₁₅ represents a cyanogroup or a halogenated alkyl group.

Advantageous Effects of Invention

According to the present invention, an organic electroluminescentelement having a low driving voltage, excellent efficiency, andexcellent durability can be provided. Further, a light emitting device,a display device, and an illumination device, each using the organicelectroluminescent element, can be provided.

In addition, according to the present invention, an iridium complex usedfor fabrication of an organic electroluminescent element having a lowdriving voltage, excellent efficiency, and excellent durability can beprovided.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic view showing one example of a configuration of anorganic electroluminescent element according to the present invention.

FIG. 2 is a schematic view showing one example of a light emittingdevice according to the present invention.

FIG. 3 is a schematic view showing one example of an illumination deviceaccording to the present invention.

FIG. 4 is a view showing ¹H-NMR data of the compound (1-7).

DESCRIPTION OF EMBODIMENTS

In the description of the general formula (1), the hydrogen atomincludes isotopes thereof (deuterium atom and the like), and the atomadditionally constituting the substituent includes isotopes thereof.

In the present invention, when referring to a “substituent”, thesubstituent may be further substituted. For example, when the “alkylgroup” is referred to in the present invention, it includes an alkylgroup substituted with a fluorine atom (for example, a trifluoromethylgroup) and an alkyl group substituted with an aryl group (for example, atriphenylmethyl group), but when “an alkyl group having 1 to 6 carbonatoms” is referred to herein, it represents any of alkyl groups having 1to 6 carbon atoms, including the alkyl groups which are substituted.

In the present invention, the Substituent Group A is defined as follows.

(Substituent Group A)

An alkyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 10carbon atoms; for example, methyl, ethyl, isopropyl, tert-butyl,n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, andcyclohexyl), an alkenyl group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 10 carbon atoms; for example, vinyl, allyl, 2-butenyl, and3-pentenyl), an alkynyl group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 10 carbon atoms; for example, propargyl and 3-pentynyl), anaryl group (preferably having 6 to 30 carbon atoms, more preferablyhaving 6 to 20 carbon atoms, and particularly preferably having 6 to 12carbon atoms; for example, phenyl, p-methylphenyl, naphthyl, andanthranyl), an amino group (preferably having 0 to 30 carbon atoms, morepreferably having 0 to 20 carbon atoms, and particularly preferablyhaving 0 to 10 carbon atoms; for example, amino, methylamino,dimethylamino, diethylamino, dibenzylamino, diphenylamino, andditolylamino), an alkoxy group (preferably having 1 to 30 carbon atoms,more preferably having 1 to 20 carbon atoms, and particularly preferablyhaving 1 to 10 carbon atoms; for example, methoxy, ethoxy, butoxy, and2-ethylhexyloxy), and an aryloxy group (preferably having 6 to 30 carbonatoms, more preferably having 6 to 20 carbon atoms, and particularlypreferably having 6 to 12 carbon atoms; for example, phenyloxy,1-naphthyloxy, and 2-naphthyloxy), a heterocyclic oxy group (preferablyhaving 1 to 30 carbon atoms, more preferably having 1 to 20 carbonatoms, and particularly preferably having 1 to 12 carbon atoms; forexample, pyridyloxy, pyrazyloxy, pyrimidyloxy, and quinolyloxy), an acylgroup (preferably having 2 to 30 carbon atoms, more preferably having 2to 20 carbon atoms, and particularly preferably having 2 to 12 carbonatoms; for example, acetyl, benzoyl, formyl, and pivaloyl), analkoxycarbonyl group (preferably having 2 to 30 carbon atoms, morepreferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 12 carbon atoms; for example, methoxycarbonyl andethoxycarbonyl), an aryloxycarbonyl group (preferably having 7 to 30carbon atoms, more preferably having 7 to 20 carbon atoms, andparticularly preferably having 7 to 12 carbon atoms; for example,phenyloxycarbonyl), an acyloxy group (preferably having 2 to 30 carbonatoms, more preferably having 2 to 20 carbon atoms, and particularlypreferably having 2 to 10 carbon atoms; for example, acetoxy andbenzoyloxy), an acylamino group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 10 carbon atoms; for example, acetylamino and benzoylamino),an alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 12 carbon atoms; for example, methoxycarbonylamino), anaryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, morepreferably having 7 to 20 carbon atoms, and particularly preferablyhaving 7 to 12 carbon atoms; for example, phenyloxycarbonylamino), asulfonylamino group (preferably having 1 to 30 carbon atoms, morepreferably having 1 to 20 carbon atoms, and particularly preferablyhaving 1 to 12 carbon atoms; for example, methanesulfonylamino andbenzenesulfonylamino), a sulfamoyl group (preferably having 0 to 30carbon atoms, more preferably having 0 to 20 carbon atoms, andparticularly preferably having 0 to 12 carbon atoms; for example,sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, and phenylsulfamoyl), acarbamoyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 12carbon atoms; for example, carbamoyl, methylcarbamoyl, diethylcarbamoyl,and phenylcarbamoyl), an alkylthio group (preferably having 1 to 30carbon atoms, more preferably having 1 to 20 carbon atoms, andparticularly preferably having 1 to 12 carbon atoms; for example,methylthio and ethylthio), an arylthio group (preferably having 6 to 30carbon atoms, more preferably having 6 to 20 carbon atoms, andparticularly preferably having 6 to 12 carbon atoms; for example,phenylthio), a heterocyclic thio group (preferably having 1 to 30 carbonatoms, more preferably having 1 to 20 carbon atoms, and particularlypreferably having 1 to 12 carbon atoms; for example, pyridylthio,2-benzoimizolylthio, 2-benzoxazolylthio, and 2-benzothiazolylthio), asulfonyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 12carbon atoms; for example, mesyl and tosyl), a sulfinyl group(preferably having 1 to 30 carbon atoms, more preferably having 1 to 20carbon atoms, and particularly preferably having to 12 carbon atoms; forexample, methanesulfinyl and benzenesulfinyl), a ureido group(preferably having 1 to 30 carbon atoms, more preferably having 1 to 20carbon atoms, and particularly preferably having 1 to 12 carbon atoms;for example, ureido, methylureido, and phenylureido), a phosphoramidegroup (preferably having 1 to 30 carbon atoms, more preferably having 1to 20 carbon atoms, and particularly preferably having 1 to 12 carbonatoms; for example, diethylphosphoramide and phenylphosphoramide), ahydroxyl group, a mercapto group, a halogen atom (for example, afluorine atom, a chlorine atom, a bromine atom, and an iodine atom), acyano group, a sulfo group, a carboxyl group, a nitro group, ahydroxamic group, a sulfino group, a hydrazino group, an imino group, aheterocyclic group (inclusive of an aromatic heterocyclic group, whichpreferably has 1 to 30 carbon atoms, and more preferably 1 to 12 carbonatoms and in which examples of the hetero atom include a nitrogen atom,an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, aselenium atom, and a tellurium atom; and specific examples thereofinclude pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl,triazolyl, imidazolyl, oxazolyl, triazolyl, isoxazolyl, isothiazolyl,quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl,piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl,benzoimidazolyl, benzothiazolyl, a carbazolyl group, an azepinyl group,and a silolyl group), a silyl group (preferably having 3 to 40 carbonatoms, more preferably having 3 to 30 carbon atoms, and particularlypreferably having 3 to 24 carbon atoms; for example, trimethylsilyl andtriphenylsilyl), a silyloxy group (preferably having 3 to 40 carbonatoms, more preferably having 3 to 30 carbon atoms, and particularlypreferably having 3 to 24 carbon atoms; for example, trimethylsilyloxyand triphenylsilyloxy), and a phosphoryl group (for example, adiphenylphosphoryl group and a dimethylphosphoryl group).

[Compound Represented by General Formula (1)]

Hereinbelow, the compound represented by the general formula (1) will bedescribed.

In the general formula (1), R₁₁₁ to R₁₃₄ each independently represent ahydrogen atom or a substituent. At least two adjacent groups out of R₁₁₁to R₁₁₄, R₁₁₄ and R₁₁₅, at least two adjacent groups out of R₁₁₅ toR₁₁₈, at least two adjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃,at least two adjacent groups out of R₁₂₃ to R₁₂₆, at least two adjacentgroups out of R₁₂₇ to R₁₃₀, R₁₃₀ and R₁₃₁, or at least two adjacentgroups out of R₁₃₁ to R₁₃₄ may be bonded to each other to form a ring,provided that at least one of R₁₁₁ to R₁₃₄ represents a grouprepresented by the following general formula (A).

In the general formula (A), X represents a cyano group or a halogenatedalkyl group. L represents a single bond or a divalent linking group. Rrepresents a substituent. In the case where a plurality of R's arepresent, they may be the same as or different from each other. nrepresents an integer of 0 to 4. * represents a binding site.

In the general formula (1), a bond between an iridium atom and anitrogen atom, and a bond between an iridium atom and a carbon atom arerepresented by solid lines, but the bonds may be covalent bonds orcoordinate bonds. Further, this also applies to the general formulae (2)to (6) as described later.

In the general formula (1), R₁₁₁ to R₁₃₄ each independently represent ahydrogen atom or a substituent. Examples of the substituent include thegroups selected from the Substituent Group A.

R₁₁₁ to R₁₃₄ are each preferably a hydrogen atom, an alkyl group, anaryl group, a heteroaryl group, or a cyano group, and for the reasonthat the durability is excellent, a hydrogen atom, an alkyl group, anaryl group, or a cyano group is more preferred, and a hydrogen atom, analkyl group, or an aryl group is still more preferred. With regard tothe alkyl group, the preferred range of the alkyl groups in theSubstituent Group A preferably includes an alkyl group having 1 to 5carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms,particularly preferably a methyl group, an ethyl group, or a propylgroup, still more preferably a methyl group or an ethyl group, and mostpreferably a methyl group. With regard to the aryl group, the preferredrange of the aryl groups in the Substituent Group A preferably includesan aryl group having 6 to 10 carbon atoms, particularly preferably aphenyl group or a naphthyl group, and most preferably a phenyl group.Preferred examples the heteroaryl group include a pyridyl group, apyrazinyl group, a pyrimidyl group, a pyridazinyl group, a pyrrolylgroup, a pyrazolyl group, a triazolyl group, an imidazolyl group, anoxazolyl group, a triazolyl group, an isoxazolyl group, and anisothiazolyl group.

In the case where R₁₁₁ to R₁₃₄ each represent a substituent, thesubstituent may be further substituted with an additional substituent,examples of the additional substituent include the groups selected fromthe Substituent Group A, and the additional substituent is preferably analkyl group, an aryl group, a heteroaryl group, or a cyano group, andmore preferably an alkyl group or an aryl group. The preferred ranges ofthe alkyl group and the aryl group as the additional substituents arethe same as the preferred ranges in the case where R₁₁₁ to R₁₃₄ asdescribed above are each an alkyl group or an aryl group. At least twoadjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, at least twoadjacent groups out of R₁₁₅ to R₁₁₈, at least two adjacent groups out ofR₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, at least two adjacent groups out of R₁₂₃ toR₁₂₆, at least two adjacent groups out of R₁₂₇ to R₁₃₀, R₁₃₀ and R₁₃₁,or at least two adjacent groups out of R₁₃₁ to R₁₃₄ may be bonded toeach other to form a ring.

From the viewpoint of obtaining light emitting materials in a yellowcolor through a red color, the aspect of forming a ring is preferably atleast one aspect selected from an aspect in which R₁₁₁ and R₁₁₂ arebonded to each other to form a ring, an aspect in which R₁₁₉ and R₁₂₀are bonded to each other to form a ring, an aspect in which R₁₂₇ andR₁₂₈ are bonded to each other to form a ring, an aspect in which R₁₁₂and R₁₁₃ are bonded to each other to form a ring, an aspect in whichR₁₂₀ and R₁₂₁ are bonded to each other to form a ring, an aspect inwhich R₁₂₈ and R₁₂₉ are bonded to each other to form a ring, an aspectin which R₁₁₃ and R₁₁₄ are bonded to each other to form a ring, anaspect in which R₁₂₁ and R₁₂₂ are bonded to each other to form a ring,and an aspect in which R₁₂₉ and R₁₃₀ are bonded to each other to form aring.

Examples of the ring thus formed include a benzene ring, a pyridinering, a pyrazine ring, a pyridazine ring, a pyrimidine ring, animidazole ring, an oxazole ring, a thiazole ring, a pyrazole ring, athiophene ring, a furan ring, and a cycloalkane ring, and preferably abenzene ring.

These rings thus formed may have a substituent, examples of thesubstituent include the Substituent Group A, and the substituent ispreferably an alkyl group, an aryl group, or a cyano group, and morepreferably an alkyl group or an aryl group.

At least one of R₁₁₁ to R₁₃₄ in general formula (1) represents a grouprepresented by the general formula (A).

The number of the groups out of R₁₁₁ to R₁₃₄ in the general formula (1)which represent a group represented by general formula (A) is preferably3 or less from the viewpoint of easiness of deposition, and morepreferably 1 to 3, more preferably 1 or 2, and still more preferably 1.

X in the general formula (A) represents a cyano group or a halogenatedalkyl group. Examples of the halogen in the halogenated alkyl groupinclude a fluorine atom, a chlorine atom, a bromine atom, and an iodineatom, and preferably a fluorine atom. As the halogenated alkyl group, afluoroalkyl group having 1 to 3 carbon atoms is preferred, and afluoroalkyl group having one carbon atom is more preferred.

From the viewpoint of improvement of the durability of an organic ELelement, X in the general formula (A) is preferably a cyano group.

L in the general formula (A) represents a single bond or a divalentlinking group. Examples of the divalent linking group include an arylenegroup or an alkylene group.

L is preferably a single bond or an arylene group. As the arylene group,an arylene group consisting of 1 to 3 benzene rings is preferred, anarylene group consisting of 1 or 2 benzene rings is more preferred, andspecifically, a phenylene group, a biphenylene group, or a terphenylenegroup is preferred, and a phenylene group or a biphenylene group isstill more preferred.

In the case where L represents an arylene group, specific examples of Linclude the following L1 to L15, and for the reason of excellent elementcharacteristics, L1, L2, L4, L5, L7, L8, L13, or L14 is preferred, andL2 or L8 is more preferred.

Furthermore, in L1 to L15 below, * represents a binding site. L1 to L15may have additional substituents.

In the case where L represents a divalent linking group, it may have asubstituent. Examples of the substituent include the groups selectedfrom the Substituent Group A, and the substituent is preferably an alkylgroup, an aryl group, or a cyano group.

R in the general formula (A) represents a substituent. Examples of thesubstituent include the groups selected from the Substituent Group A,and the substituent is preferably an alkyl group, an aryl group, or acyano group, more preferably an alkyl group or an aryl group, and stillmore preferably an aryl group. The preferred ranges of the alkyl groupand the aryl group as the substituent are the same as the preferredranges in the case where R₁₁₁ to R₁₃₄ as described above are each analkyl group or an aryl group.

R may be substituted with another substituent, examples of thesubstituent include the groups selected from the Substituent Group A,and the substituent is preferably an alkyl group, an aryl group, aheteroaryl group, or a cyano group, more preferably an alkyl group or anaryl group, and still more preferably an aryl group.

n in the general formula (A) represents an integer of 0 to 4. n ispreferably an integer of 0 to 3, more preferably an integer of 0 to 2,still more preferably 0 or 1, and particularly preferably 0.

The group represented by the general formula (A) is preferablysubstituted with two or less groups selected from R₁₁₆, R₁₂₄, and R₁₃₂,two or less groups selected from R₁₁₃, R₁₂₁, and R₁₂₉, two or lessgroups selected from R₁₁₂, R₁₂₀, and R₁₂₈, or two or less groupsselected from R₁₁₇, R₁₂₅, and R₁₃₃; more preferably substituted with twoor less groups selected from R₁₁₆, R₁₂₄, and R₁₃₂, two or less groupsselected from R₁₁₃, R₁₂₁, and R₁₂₉, or two or less groups selected fromR₁₁₇, R₁₂₅, and R₁₃₃; and still more preferably substituted with two orless groups selected from R₁₁₆, R₁₂₄, and R₁₃₂, or two or less groupsselected from R₁₁₇, R₁₂₅, and R₁₃₃, in the general formula (1).

From the viewpoint of excellent durability, the compound represented bythe general formula (1) is preferably a compound represented by any oneof the following general formulae (2) to (6); and from the viewpoint ofeasiness of deposition, the compound represented by the general formula(1) is more preferably a compound represented by the following generalformula (2), (4), or (6), still more preferably a compound representedby the following general formula (2) or (4), and particularly preferablya compound represented by the following general formula (2).

In the general formula (2), R₁₁₁ to R₁₂₃, R₁₂₅, R₁₂₆, and R₂₁₁ to R₂₁₅each independently represent a hydrogen atom or a substituent. Twogroups out of R₁₁₁ to R₁₁₈ may be each the same as or different fromeach other. At least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ andR₁₁₅, at least two adjacent groups out of R₁₁₅ to R₁₁₈, at least twoadjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, R₁₂₅ and R₁₂₆, or atleast two adjacent groups out of R₂₁₁ to R₂₁₅ may be bonded to eachother to form a ring. L represents a single bond or a divalent linkinggroup, provided that at least one of R₂₁₁ to R₂₁₅ represents a cyanogroup or a halogenated alkyl group.

In the general formula (2), the specific examples and the preferredranges of R₁₁₁ to R₁₂₃, R₁₂₅, R₁₂₆, and R₂₁₁ to R₂₁₅ are the same asthose of R₁₁₁ to R₁₃₄ in the general formula (1), and the specificexamples and the preferred ranges of the additional substituents in thecase where R₁₁₁ to R₁₂₃, R₁₂₅, R₁₂₆, and R₂₁₁ to R₂₁₅ represent asubstituent are also the same as the specific examples and the preferredranges of the additional substituents in the case where R₁₁₁ to R₁₃₄ inthe general formula (1) represent a substituent.

In the general formula (2), R₁₁₁ to R₁₁₈ are each present in pairs, buteach of them may be each the same as or different from each other, andare preferably the same as each other for the easiness of synthesis.

At least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, atleast two adjacent groups out of R₁₁₅ to R₁₁₈, at least two adjacentgroups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, R₁₂₅ and R₁₂₆, or at leasttwo adjacent groups out of R₂₁₁ to R₂₁₅ may be bonded to each other toform a ring.

From the viewpoint of obtaining yellow through red light emittingmaterials, at least one aspect selected from an aspect where R₁₁₁ andR₁₁₂ are bonded to each other to form a ring, an aspect where R₁₁₉ andR₁₂₀ are bonded to each other to form a ring, an aspect where R₁₁₂ andR₁₁₃ are bonded to each other to form a ring, an aspect where R₁₂₀ andR₁₂₁ are bonded to each other to form a ring, an aspect where R₁₁₃ andR₁₁₄ are bonded to each other to form a ring, and an aspect where R₁₂₁and R₁₂₂ are bonded to each other to form a ring is preferred.

The specific examples and the preferred ranges of the ring thus formedare the same as specific examples and the preferred ranges of the ringin the case where R₁₁₁ to R₁₃₄ in the general formula (1) form a ring.Further, the ring may have a substituent, and the specific examples andthe preferred range of the substituent are the same as described in thegeneral formula (1).

In the general formula (2), L represents a single bond or a divalentlinking group, and the specific examples and the preferred range of Lare the same as the specific examples and the preferred range of L inthe general formula (1), and a single bond or a phenylene group isparticularly preferred. Further, the substituent which L may have is thesame as described in the general formula (1).

At least one of R₂₁₁ to R₂₁₅ in the general formula (2) represents acyano group or a halogenated alkyl group, or preferably a cyano group.

The number of groups out of R₂₁₁ to R₂₁₅ in the general formula (2),which represent a cyano group or a halogenated alkyl group, ispreferably 1 to 3, more preferably 1 to 2, and still more preferably 1.

The groups other than the cyano group or the halogenated alkyl group outof R₂₁₁ to R₂₁₅ in the general formula (2) is preferably a hydrogenatom, an alkyl group, or an aryl group, more preferably a hydrogen atomor an aryl group, and still more preferably a hydrogen atom.

A case where the compound represented by the general formula (1) is acompound represented by the following general formula (3) is alsopreferred.

In the general formula (3), R₁₁₁ to R₁₁₅, R₁₁₇, R₁₁₈, R₁₁₉ to R₁₂₆, andR₃₁₁ to R₃₁₅ each independently represent a hydrogen atom or asubstituent. Two groups out of R₁₁₁ to R₁₁₅, R₁₁₇, R₁₁₈, and R₃₁₁ toR₃₁₅ may be each the same as or different from each other. At least twoadjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, R₁₁₇ and R₁₁₈, atleast two adjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, at leasttwo adjacent groups out of R₁₂₃ to R₁₂₆, or at least two adjacent groupsout of R₃₁₁ to R₃₁₅ may be bonded to each other to form a ring. Lrepresents a single bond or a divalent linking group, provided that atleast one of R₃₁₁ to R₃₁₅ represents a cyano group or a halogenatedalkyl group.

In the general formula (3), the specific examples and the preferredranges of R₁₁₁ to R₁₁₅, R₁₁₇, R₁₁₈, R₁₁₉ to R₁₂₆, and R₃₁₁ to R₃₁₅ arethe same as those of R₁₁₁ to R₁₃₄ in the general formula (1); thespecific examples and the preferred ranges of the additionalsubstituents which may be contained in the case where R₁₁₁ to R₁₁₅,R₁₁₇, R₁₁₈, R₁₁₉ to R₁₂₆, and R₃₁₁ to R₃₁₅ represent substituents arethe same as the specific examples and the preferred ranges of theadditional substituents in the case where R₁₁₁ to R₁₃₄ in the generalformula (1) represent substituents.

In the general formula (3), R₁₁₁ to R₁₁₅, R₁₁₇, R₁₁₈, and R₃₁₁ to R₃₁₅are present in pairs, but they may be each the same as or different fromeach other, and are preferably the same as each other for the easinessof synthesis.

At least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, R₁₁₇and R₁₁₈, at least two adjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ andR₁₂₃, at least two adjacent groups out of R₁₂₃ to R₁₂₆, or at least twoadjacent groups out of R₃₁₁ to R₃₁₅ may be bonded to each other to forma ring.

The specific examples and the preferred range of the ring thus formedare the same as the specific examples and the preferred range of thering in the case where R₁₁₁ to R₁₃₄ in the general formula (1) form aring. Further, the ring may have a substituent, and the specificexamples and the preferred range of the substituent are the same asdescribed in the general formula (1).

In the general formula (3), L represents a single bond or a divalentlinking group, the specific examples and the preferred range of L arethe same as the specific examples and the preferred range of L in thegeneral formula (1), and a single bond or a phenylene group isparticularly preferred. Further, the substituents which L may have arealso the same as described in the general formula (1).

At least one of R₃₁₁ to R₃₁₅ in the general formula (3) represents acyano group or a halogenated alkyl group, and preferably a cyano group.

The number of groups out of R₃₁₁ to R₃₁₅ in the general formula (3),which represent a cyano group or a halogenated alkyl group, ispreferably 1 to 3, more preferably 1 to 2, and still more preferably 1.

The groups other than the cyano group or the halogenated alkyl group outof R₃₁₁ to R₃₁₅ in the general formula (3) is preferably a hydrogenatom, an alkyl group, or an aryl group, more preferably a hydrogen atomor an aryl group, and still more preferably a hydrogen atom.

Also preferred is a case where the compound represented by the generalformula (1) is a compound represented by the following general formula(4).

In the general formula (4), R₁₁₁ to R₁₂₀, R₁₂₂ to R₁₂₆, and R₄₁₁ to R₄₁₅each independently represent a hydrogen atom or a substituent. Twogroups out of R₁₁₁ to R₁₁₈ may be each the same as or different fromeach other. At least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ andR₁₁₅, at least two adjacent groups out of R₁₁₅ to R₁₁₈, R₁₁₉ and R₁₂₀,R₁₂₂ and R₁₂₃, at least two adjacent groups out of R₁₂₃ to R₁₂₆, or atleast two adjacent groups out of R₄₁₁ to R₄₁₅ may be bonded to eachother to form a ring. L represents a single bond or a divalent linkinggroup, provided that at least one of R₄₁₁ to R₄₁₅ represents a cyanogroup or a halogenated alkyl group.

In the general formula (4), the specific examples and the preferredranges of R₁₁₁ to R₁₂₀, R₁₂₂ to R₁₂₆, and R₄₁₁ to R₄₁₅ are the same asthose of R₁₁₁ to R₁₃₄ in the general formula (1), and the specificexamples and the preferred ranges of the additional substituents in thecase where R₁₁₁ to R₁₂₀, R₁₂₂ to R₁₂₆, and R₄₁₁ to R₄₁₅ represent asubstituent are also the same as the specific examples and the preferredranges of the additional substituents in the case where R₁₁₁ to R₁₃₄ inthe general formula (1) represent a substituent.

In the general formula (4), R₁₁₁ to R₁₁₈ are present in pairs, but eachof them may be each the same as or different from each other, and arepreferably the same as each other for the easiness of synthesis.

At least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, atleast two adjacent groups out of R₁₁₅ to R₁₁₈, R₁₁₉ and R₁₂₀, R₁₂₂ andR₁₂₃, at least two adjacent groups out of R₁₂₃ to R₁₂₆, and at least twoadjacent groups out of R₄₁₁ to R₄₁₅ may be bonded to each other to forma ring.

The specific examples and the preferred range of the ring thus formedare the same as the specific examples and the preferred range of thering in the case where R₁₁₁ to R₁₃₄ in the general formula (1) form aring. Further, the ring may have a substituent, and the specificexamples and the preferred range of the substituent are the same asdescribed in the general formula (1).

In the general formula (4), L represents a single bond or a divalentlinking group, the specific examples and the preferred range of L arethe same as the specific examples and the preferred range of L in thegeneral formula (1), and a single bond or a phenylene group isparticularly preferred. Further, the substituents which L may have arealso the same as described in the general formula (1).

At least one of R₄₁₁ to R₄₁₅ in the general formula (4) represents acyano group or a halogenated alkyl group, or preferably a cyano group.

The number of groups out of R₄₁₁ to R₄₁₅ in the general formula (4),which represent a cyano group or a halogenated alkyl group, ispreferably 1 to 3, more preferably 1 to 2, and still more preferably 1.

The groups other than the cyano group or the halogenated alkyl group outof R₄₁₁ to R₄₁₅ in the general formula (4) is preferably a hydrogenatom, an alkyl group, or an aryl group, more preferably a hydrogen atomor an aryl group, and still more preferably a hydrogen atom.

Also preferred is a case where the compound represented by the generalformula (1) is a compound represented by the following general formula(5).

In the general formula (5), R₁₁₁, R₁₁₂, R₁₁₄, R₁₁₅ to R₁₂₆, and R₅₁₁ toR₅₁₅ each independently represent a hydrogen atom or a substituent. Twogroups out of R₁₁₁, R₁₁₂, R₁₁₄, R₁₁₅ to R₁₁₈, and R₅₁₁ to R₅₁₅ may beeach the same as or different from each other. R₁₁₁ and R₁₁₂, R₁₁₄ andR₁₁₅, at least two adjacent groups out of R₁₁₅ to R₁₁₈, at least twoadjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, at least twoadjacent groups out of R₁₂₃ to R₁₂₆, or at least two adjacent groups outof R₅₁₁ to R₅₁₅ may be bonded to each other to form a ring. L representsa single bond or a divalent linking group, provided that at least one ofR₅₁₁ to R₅₁₅ represents a cyano group or a halogenated alkyl group.

In the general formula (5), the specific examples and the preferredranges of R₁₁₁, R₁₁₂, R₁₁₄, R₁₁₅ to R₁₂₆, and R₅₁₁ to R₅₁₅ are the sameas those of R₁₁₁ to R₁₃₄ in the general formula (1), and the specificexamples and the preferred ranges of the additional substituents in thecase where R₁₁₁, R₁₁₂, R₁₁₄, R₁₁₅ to R₁₂₆, and R₅₁₁ to R₅₁₅ represent asubstituent are also the same as the specific examples and the preferredranges of the additional substituents in the case where R₁₁₁ to R₁₃₄ inthe general formula (1) represent a substituent.

In the general formula (5), R₁₁₁, R₁₁₂, R₁₁₄, R₁₁₅ to R₁₁₈, and R₅₁₁ toR₅₁₅ are each present in pairs, but each of them may be each the same asor different from each other, and are preferably the same as each otherfor the easiness of synthesis.

R₁₁₁ and R₁₁₂, R₁₁₄ and R₁₁₅, at least two adjacent groups out of R₁₁₅to R₁₁₈, at least two adjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ andR₁₂₃, at least two adjacent groups out of R₁₂₃ to R₁₂₆, or at least twoadjacent groups out of R₅₁₁ to R₅₁₅ may be bonded to each other to forma ring.

The specific examples and the preferred range of the ring thus formedare the same as the specific examples and the preferred range of thering in the case where R₁₁₁ to R₁₃₄ in the general formula (1) form aring. Further, the ring may have a substituent, and the specificexamples and the preferred range of the substituent are the same asdescribed in the general formula (1).

In the general formula (5), L represents a single bond or a divalentlinking group, the specific examples and the preferred range of L arethe same as the specific examples and the preferred range of L in thegeneral formula (1), and a single bond or a phenylene group isparticularly preferred. Further, the substituents which L may have arealso the same as described in the general formula (1).

At least one of R₅₁₁ to R₅₁₅ in the general formula (5) represents acyano group or a halogenated alkyl group, or preferably a cyano group.

The number of groups out of R₅₁₁ to R₅₁₅ in the general formula (5),which represent a cyano group or a halogenated alkyl group, ispreferably 1 to 3, more preferably 1 to 2, and still more preferably 1.

The groups other than the cyano group or the halogenated alkyl group outof R₅₁₁ to R₅₁₅ in the general formula (5) is preferably a hydrogenatom, an alkyl group, or an aryl group, more preferably a hydrogen atomor an aryl group, and still more preferably a hydrogen atom.

Also preferred is a case where the compound represented by the generalformula (1) is a compound represented by the following general formula(6).

In the general formula (6), R₁₁₁ to R₁₂₄, R₁₂₆, and R₆₁₁ to R₆₁₅ eachindependently represent a hydrogen atom or a substituent. Two groups outof R₁₁₁ to R₁₁₈ may be each the same as or different from each other. Atleast two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, at leasttwo adjacent groups out of R₁₁₅ to R₁₁₈, at least two adjacent groupsout of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, R₁₂₃ and R₁₂₄, or at least twoadjacent groups out of R₆₁₁ to R₆₁₅ may be bonded to each other to forma ring. L represents a single bond or a divalent linking group, providedthat at least one of R₆₁₁ to R₆₁₅ represents a cyano group or ahalogenated alkyl group.

In the general formula (6), the specific examples and the preferredranges of R₁₁₁ to R₁₂₄, R₁₂₆, and R₆₁₁ to R₆₁₅ are the same as those ofR₁₁₁ to R₁₃₄ in the general formula (1), and the specific examples andthe preferred ranges of the additional substituents in the case whereR₁₁₁ to R₁₂₄, R₁₂₆, and R₆₁₁ to R₆₁₅ represent a substituent are alsothe same as the specific examples and the preferred ranges of theadditional substituents in the case where R₁₁₁ to R₁₃₄ in the generalformula (1) represent a substituent.

In the general formula (6), R₁₁₁ to R₁₁₈ are each present in pairs, buteach of them may be each the same as or different from each other, andare preferably the same as each other for the easiness of synthesis.

At least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, atleast two adjacent groups out of R₁₁₅ to R₁₁₈, at least two adjacentgroups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, R₁₂₃ and R₁₂₄, or at leasttwo adjacent groups out of R₆₁₁ to R₆₁₅ may be bonded to each other toform a ring.

The specific examples and the preferred ranges of the ring thus formedare the same as specific examples and the preferred ranges of the ringin the case where R₁₁₁ to R₁₃₄ in the general formula (1) form a ring.Further, the ring may have a substituent, and the specific examples andthe preferred range of the substituent are the same as described in thegeneral formula (1).

In the general formula (6), L represents a single bond or a divalentlinking group, the specific examples and the preferred range of L arethe same as the specific examples and the preferred range of L in thegeneral formula (1), and a single bond or a phenylene group isparticularly preferred. Further, the substituents which L may have arealso the same as described in the general formula (1).

At least one of R₆₁₁ to R₆₁₅ in the general formula (6) represents acyano group or a halogenated alkyl group, or preferably a cyano group.

The number of groups out of R₆₁₁ to R₆₁₅ in the general formula (6),which represent a cyano group or a halogenated alkyl group, ispreferably 1 to 3, more preferably 1 to 2, and still more preferably 1.

The groups other than the cyano group or the halogenated alkyl group outof R₆₁₁ to R₆₁₅ in the general formula (6) is preferably a hydrogenatom, an alkyl group, or an aryl group, more preferably a hydrogen atomor an aryl group, and still more preferably a hydrogen atom.

The molecular weight of the compound represented by the general formula(1) is preferably 400 to 1000, and more preferably 450 to 900, from theviewpoint of the sublimation suitability.

The glass transition temperature (Tg) of the compound represented by thegeneral formula (1) is preferably 80° C. or higher, more preferably 90°C. or higher, still more preferably 100° C. or higher, and particularlypreferably 110° C. or higher, from the viewpoint of stable operationduring driving of an organic electroluminescent element at a hightemperature or against heat generation during driving of the element.

Specific examples of the compound represented by the general formula (1)are listed below, but the present invention is not limited thereto.

The compound represented by the general formula (1) can be synthesizedby the method described in WO2009/073245, WO2010/028151, or the like.

The present invention also relates to a compound represented by thegeneral formula (1) (further, a compound represented by the generalformula (2), (3), (4), (5) or (6)).

The compound represented by the general formula (1) is not limited interms of its uses and may be contained in any organic layers of theorganic electroluminescent element, but the layer to which the compoundrepresented by the general formula (1) is introduced is preferably alight emitting layer, and particularly preferably used as a lightemitting material.

[Light Emitting Material Represented by General Formula (1)]

The present invention also relates to a light emitting materialrepresented by the general formula (1).

The compound represented by the general formula (1) and the lightemitting material of the present invention can be preferably used fororganic electronic elements such as electrophotographs, organictransistors, organic photoelectric conversion elements (energyconversion applications, sensor applications, or the like), and organicelectroluminescent elements, and particularly preferably used fororganic electroluminescent elements.

[Thin Film Containing Compound Represented by General Formula (1)]

The present invention also relates to a thin film containing thecompound represented by the general formula (1). The thin film of thepresent invention can be formed by any of dry film forming methods suchas a deposition method and a sputtering method, and wet type filmforming methods such as a transfer method and a printing method. Thefilm thickness of the thin film can be any one, depending on the uses,but is preferably 0.1 nm to 1 mm, more preferably 0.5 nm to 1 μm, stillmore preferably 1 nm to 200 nm, and particularly preferably 1 nm to 100nm.

[Organic Electroluminescent Element]

The organic electroluminescent element of the present invention is anorganic electroluminescent element including a substrate, a pair ofelectrodes including an anode and a cathode, disposed on the substrate,and at least one organic layer including a light emitting layer,disposed between the electrodes, in which at least one kind of compoundrepresented by the following general formula (1) is contained in anylayer of the at least one organic layer. In view of the properties ofthe organic electroluminescent element, at least one electrode of a pairof electrodes, the anode and the cathode, is preferably transparent orsemi-transparent.

Examples of the organic layer other than the light emitting layerinclude a hole injecting layer, a hole transporting layer, a blockinglayer (a hole blocking layer, an exciton blocking layer, and the like),an electron transporting layer, and an electron injecting layer. Theseorganic layers may be provided as a single layer or a plurality oflayers, and in the case where a plurality of layers are provided, theymay be formed of the same materials or different materials in everylayer.

FIG. 1 shows one example of the configuration of the organicelectroluminescent element according to the present invention. Theorganic electroluminescent element 10 in FIG. 1 has an organic layerincluding a light emitting layer 6 between a pair of electrodes (ananode 3 and a cathode 9) on a substrate 2. A hole injecting layer 4, ahole transporting layer 5, a light emitting layer 6, a hole blockinglayer 7, and an electron transporting layer 8 are laminated in thisorder as the organic layer from the anode 3 side.

<Configuration of Organic Layer>

The layer configuration of the organic layer is not particularly limitedand can be suitably selected depending on the use and purpose of theorganic electroluminescent element. However, the organic layer ispreferably formed on a transparent electrode or a semi-transparentelectrode. In that case, the organic layer is formed on the entiresurface or the partial surface of the transparent electrode or thesemi-transparent electrode.

The shape, the size, the thickness, and the like of the organic layerare not particularly limited and can be suitably selected depending onthe purpose.

Specific examples of the layer configuration include the following, butthe present invention is not limited to these configurations.

-   -   Anode/light emitting layer/cathode    -   Anode/hole transporting layer/light emitting layer/cathode    -   Anode/light emitting layer/electron transporting layer/cathode    -   Anode/hole transporting layer/light emitting layer/electron        transporting layer/cathode    -   Anode/hole transporting layer/light emitting layer/blocking        layer/electron transporting layer/cathode    -   Anode/hole transporting layer/light emitting layer/blocking        layer/electron transporting layer/electron injecting        layer/cathode    -   Anode/hole injecting layer/hole transporting layer/light        emitting layer/blocking layer/electron transporting        layer/cathode    -   Anode/hole injecting layer/hole transporting layer/light        emitting layer/electron transporting layer/electron injecting        layer/cathode    -   Anode/hole injecting layer/hole transporting layer/light        emitting layer/blocking layer/electron transporting        layer/electron injecting layer/cathode    -   Anode/hole injecting layer/hole transporting layer/blocking        layer/light emitting layer/blocking layer/electron transporting        layer/electron injecting layer/cathode

The element configuration, the substrate, the cathode, and the anode ofthe organic electroluminescent element are described in detail in, forexample, JP-A-2008-270736, and the detailed descriptions in thepublication can be applied to the present invention.

<Substrate>

The substrate used in the present invention is preferably a substratethat does not scatter or decay light emitted from the organic layer. Inthe case of an organic material, those having excellent heat resistance,dimensional stability, solvent resistance, electrical insulatingproperties, and processability are preferred.

<Anode>

The anode may be usually one having a function as an electrode ofsupplying holes into an organic layer, and is not particularly limitedin terms of its shape, structure, size, or the like. Further, dependingon the use and purpose of the light emitting element, the anode can besuitably selected from the known electrode materials. As describedabove, the anode is usually provided as a transparent anode.

<Cathode>

The cathode may be usually one having a function as an electrode ofinjecting electrons to an organic layer, and is not particularly limitedin terms of its shape, structure, size, or the like. Further, dependingon the use and purpose of the light emitting element, the cathode can besuitably selected from the known electrode materials.

<Organic Layer>

The organic layer of the present invention will be described.

(Formation Organic Layer)

The respective organic layers in the organic electroluminescent elementof the present invention can be suitably formed by any of dry filmforming methods such as a deposition method and a sputtering method, andsolution coating methods such as a transfer method, a printing method, aspin coating method, and a bar coating method.

(Light Emitting Layer)

The light emitting layer is a layer having a function of, uponapplication of an electric field, receiving holes from the anode, thehole injecting layer, or the hole transporting layer, receivingelectrons from the cathode, the electron injecting layer, or theelectron transporting layer, providing a recombination site of the holesand the electrons, and causing light emitting.

(Light Emitting Material)

In the present invention, at least one kind of light emitting materialis preferably contained in the light emitting layer, and more preferablyat least one kind of phosphorescent light emitting material in the lightemitting layer. As the phosphorescent light emitting material, thecompound represented by the general formula (1) is preferred.

In the present invention, a fluorescent light emitting material or aphosphorescent light emitting material different from the compoundrepresented by the general formula (1) can be used, in addition to thecompound represented by the general formula (1), as the light emittingmaterial in the light emitting layer.

The fluorescent light emitting materials or the phosphorescent lightemitting materials are described in detail in, for example, paragraphNos. [0100] to [0164] of JP-A-2008-270736 and paragraph Nos. [0088] to[0090] of JP-A-2007-266458, and the detailed descriptions in thesepublications can be applied to the present invention.

Examples of the phosphorescent light emitting material which can be usedin the present invention include phosphorescent light emitting materialsdescribed in Patent Literatures, for example, U.S. Pat. Nos.6,303,238B1, 6,097,147, WO00/57676, WO00/70655, WO01/08230,WO01/39234A2, WO01/41512A1, WO02/02714A2, WO02/15645A1, WO02/44189A1,WO05/19373A2, JP-A-2001-247859, JP-A-2002-302671, JP-A-2002-117978,JP-A-2003-133074, JP-A-2002-235076, JP-A-2003-123982, JP-A-2002-170684,EP1211257, JP-A-2002-226495, JP-A-2002-234894, JP-A-2001-247859,JP-A-2001-298470, JP-A-2002-173674, JP-A-2002-203678, JP-A-2002-203679,JP-A-2004-357791, JP-A-2006-256999, JP-A-2007-19462, JP-A-2007-84635,and JP-A-2007-96259. Above all, examples of the light emitting materialwhich is more preferred include phosphorescent light emitting metalcomplex compounds such as Ir complexes, Pt complexes, Cu complexes, Recomplexes, W complexes, Rh complexes, Ru complexes, Pd complexes, Oscomplexes, Eu complexes, Tb complexes, Gd complexes, Dy complexes, andCe complexes, with Ir complexes, Pt complexes, and Re complexes beingparticularly preferred. Above all, Ir complexes, Pt complexes, and Recomplexes each including at least one coordination mode of ametal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and ametal-sulfur bond are preferred. Furthermore, from the viewpoints ofluminous efficiency, driving durability, and chromaticity, Ir complexesand Pt complexes are particularly preferred, and Ir complexes are themost preferred.

These phosphorescent light emitting metal complex compounds arepreferably contained in the light emitting layer, together with thecompound represented by the general formula (1).

The compound represented by the general formula (1) in the lightemitting layer is preferably contained in the amount of 0.1% by mass to50% by mass, based on the total mass of the compound forming the lightemitting layer, and from the viewpoints of durability and externalquantum efficiency, it is preferably contained in the amount of 1% bymass to 50% by mass, and more preferably in the amount of 2% by mass to40% by mass.

The thickness of the light emitting layer is not particularly limited,but it is usually from 2 nm to 500 nm, and above all, from the viewpointof external quantum efficiency, it is more preferably from 3 nm to 200nm, and still more preferably from 5 nm to 100 nm.

The light emitting layer in the element of the present invention may beconstituted of only the light emitting material or may be constituted asa mixed layer of a host material and the light emitting material. Thelight emitting material may be made of a single kind or two or morekinds thereof. The host material is preferably a charge transportingmaterial. The host material may be made of a single kind or two or morekinds thereof. Examples thereof include a configuration in which anelectron transporting host material and a hole transporting hostmaterial are mixed. Further, the light emitting layer may include amaterial which does not have charge transporting properties and does notemit light.

In addition, the light emitting layer may be made of a single layer ormultiple layers of two or more layers. The respective layers may includethe same light emitting material or host material, and may also includea different material in every layer. In the case where a plurality oflight emitting layers are present, the respective light emitting layersmay emit light in a different luminous color from each other.

(Host Material)

The host material is a compound that usually plays a role in injectingor transporting charges in the light emitting layer and is also acompound which does not substantially emit light in itself. As usedherein, the phrase “which does not substantially emit light” means thatthe amount of light emitting from the compound which does notsubstantially emit light is preferably 5% or less, more preferably 3% orless, and still more preferably 1% or less of the total amount of lightemitting in the whole of the element.

Examples of the host material include compounds having the followingstructures in the partial structures: conductive high-molecularoligomers such as aromatic hydrocarbon, pyrrole, indole, carbazole,azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole,imidazole, thiophene, dibenzothiophene, polyarylalkane, pyrazoline,pyrazolone, phenylenediamine, arylamine, amino-substituted chalcone,styrylanthracene, hydrazone, stilbene, silazane, aromatic tertiary aminecompounds, styrylamine compounds, porphyrin-based compounds,polysilane-based compounds, poly(N-vinylcarbazole), aniline-basedcopolymers, thiophene oligomers, and polythiophene, organic silanes,carbon films, pyridine, pyrimidine, triazine, oxadiazole, fluorenone,anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide,carbodiimide, fluorenylidenemethane, distyrylpyrazine,fluorine-substituted aromatic compounds, heterocyclic tetracarboxylicanhydrides such as naphthalene perylene, phthalocyanine, and a varietyof metal complexes typified by metal complexes of 8-quinolinolderivatives and metal complexes having metal phthalocyanine,benzoxazole, or benzothiazole as a ligand thereof, and derivativesthereof (which may have a substituent or a fused ring).

The organic electroluminescent element of the present inventionpreferably contains the compound represented by the general formula (1)and a compound having a cyano group, and more preferably contains thecompound represented by the general formula (1) as the light emittingmaterial and a compound having a cyano group as a host material.

Preferred examples of the host material include carbazole derivatives,dibenzofuran derivatives, dibenzothiophene derivatives, and triphenylenederivatives.

As the dibenzofuran derivatives and the dibenzothiophene derivatives,the compounds represented by the following general formula (S-1) arepreferred.

In the general formula (S-1), X represents an oxygen atom or a sulfuratom. R₁₀₁ to R₁₀₇ each independently represent a hydrogen atom or asubstituent, and R₁₀₈ represents a substituent. a represents an integerof 0 to 4. n represents an integer of 1 or more. La represents ann-valent aromatic hydrocarbon groups and may have a substituent.

X represents an oxygen atom or a sulfur atom.

Examples of the substituents represented by R₁₀₁ to R₁₀₈ eachindependently represent the Substituent Group A. The substituents mayfurther have a substituent, and examples of the additional substituentinclude the groups selected from the Substituent Group A.

As R₁₀₁ to R₁₀₇, a hydrogen atom, an alkyl group, a cyano group, or anaryl group is preferred.

n represents an integer of 1 or more, preferably 1 to 3, more preferably1 or 2, and still more preferably 2. In the case where n represents aninteger of 2 or more, each of the X, R₁₀₁ to R₁₀₈, and a which arepresent in plural in the general formula (S-1) may be different fromeach other.

La represents an n-valent aromatic hydrocarbon group, examples of thearomatic hydrocarbon group include a phenyl group, a fluorenyl group, anaphthyl group, and a triphenylenyl group, but a group formed by thelinkage of 1 to 3 benzene rings being preferred, which includes L1 toL15 described as the specific examples of L in the general formula (A).

La may further have a substituent. Examples of the substituent in thecase where La has an additional substituent include the SubstituentGroup A; preferably a cyano group, a substituted or unsubstituted arylgroup (a phenyl group or a biphenyl group), a heterocyclic group(preferably a nitrogen-containing aromatic heterocyclic group, and morepreferably a carbazolyl group, an acridinyl group, and the like), or adiarylamino group (as the aryl group, a phenyl group is preferred, andthe aryl groups may be bonded to each other or the aryl group may bebonded to La to form a ring); more preferably a cyano group or asubstituted or unsubstituted aryl group (a phenyl group or a biphenylgroup); still more preferably a cyano group or a phenyl group; andparticularly preferably a cyano group. The substituent in the case wherethe aryl group has a substituent is preferably a cyano group or a phenylgroup.

From the viewpoint of durability, at least one cyano group is preferablycontained in the general formula (S-1). Further, from the viewpoint ofthe chemical stability of charge transporting molecules, it ispreferable that a cyano group be only a substituent of R₁₀₈ or La, andfrom the same viewpoint, it is preferable that a cyano group be only asubstituent of La.

Specific examples of the compound represented by general formula (S-1)are listed below, but are not limited thereto.

Examples of the triphenylene derivative include a compound representedby the following general formula (Tp-1).

In the general formula (Tp-1), R¹² to R²³ each independently represent ahydrogen atom, an alkyl group, or a phenyl group which may besubstituted with an alkyl group, a phenyl group, a fluorenyl group, anaphthyl group, or a triphenylenyl group, a fluorenyl group, a naphthylgroup, or a triphenylenyl group. However, there is no case where R¹² toR²³ are all hydrogen atoms.

Examples of the alkyl group represented by R¹² to R²³ include a methylgroup, an ethyl group, an isopropyl group, an n-butyl group, atert-butyl group, an n-octyl group, an n-decyl group, an n-hexadecylgroup, a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group,each of which is substituted or unsubstituted; preferably a methylgroup, an ethyl group, an isopropyl group, a tert-butyl group, and acyclohexyl group; and more preferably a methyl group, an ethyl group,and a tert-butyl group.

As R¹² to R²³, an alkyl group having 1 to 4 carbon atoms, a phenylgroup, a fluorenyl group, a naphthyl group, or a triphenylenyl group,which may be substituted with an alkyl group having 1 to 4 carbon atoms,a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenylgroup (there may be further substituted with an alkyl group, a phenylgroup, a fluorenyl group, a naphthyl group, or a triphenylenyl group) isstill more preferred; and

benzene rings which may be substituted with a phenyl group, a fluorenylgroup, a naphthyl group, or a triphenylenyl group (these may be furthersubstituted with an alkyl group, a phenyl group, a fluorenyl group, anaphthyl group, or a triphenylenyl group) are particularly preferred.

The total number of the aryl rings in the general formula (Tp-1) ispreferably from 2 to 8, and preferably from 3 to 5. With the number inthese ranges, a good amorphous thin film can be formed, and thus, thesolubility in a solvent, and the sublimation and deposition suitabilitybecome better.

R¹² to R²³ each independently have a total number of carbon atoms ofpreferably from 20 to 50, and more preferably from 20 to 36. Withinthese ranges, an amorphous thin film with good quality can be formed andthus, the solubility in a solvent, and the sublimation and depositionsuitability become better.

Hereinbelow, specific examples of the compound represented by thegeneral formula (Tp-1) are shown below, but are not limited thereto.

The compounds can be synthesized by the methods described inWO05/013388, WO06/130598, WO09/021107, US2009/0009065, WO09/008311, andWO04/018587.

(Charge Transporting Layer)

The charge transporting layer refers to a layer in which charges movewhen voltage is applied to the organic electroluminescent element.Specific examples thereof include a hole injecting layer, a holetransporting layer, an electron blocking layer, a light emitting layer,a hole blocking layer, an electron transporting layer, and an electroninjecting layer. When the charge transporting layer is a hole injectinglayer, a hole transporting layer, an electron blocking layer, or a lightemitting layer, which is formed by a coating method, it becomes possibleto prepare an organic electroluminescent element with low cost and highefficiency.

(Hole Injecting Layer and Hole Transporting Layer)

The hole injecting layer and the hole transporting layer are layershaving a function of receiving holes from the anode or the anode sideand transporting them to the cathode side.

In addition, with respect to the hole injecting layer and the holetransporting layer, the detailed descriptions in paragraph Nos. [0165]to [0167] of JP-A-2008-270736 can be applied to the present invention.

Further, the following compounds can also be preferably used as a holeinjecting material.

The hole injecting layer preferably contains an electron receptivedopant. By incorporating the electron receptive dopant in the holeinjecting layer, there are effects in which, for example, the holeinjecting properties are improved, the driving voltage is lowered, andthe efficiency is improved. The electron receptive dopant may be any oneof organic materials and inorganic materials as long as it is capable ofwithdrawing electrons from a material to be doped and generating radicalcations, and examples thereof include tetracyanoquinodimethane (TCNQ),tetrafluorotetracyanoquinodimethane (F₄-TCNQ), and molybdenum oxide.

The electron receptive dopant in the hole injecting layer is containedin the amount of preferably from 0.01% by mass to 50% by mass, morepreferably from 0.1% by mass to 40% by mass, and still more preferablyfrom 0.2% by mass to 30% by mass, with respect to the total mass of thecompounds forming the hole injecting layer.

(Charge Generating Layer)

As the compound which forms the charge generating layer, the samecompounds as the compounds used in the hole injecting layer can be used.

(Electron Injecting Layer and Electron Transporting Layer)

The electron injecting layer and the electron transporting layer arelayers having a function of receiving electrons from the cathode or thecathode side and transporting them to the anode side. The electroninjecting material and the electron transporting material used in theselayers may be either a low-molecular compound or a high-molecularcompound.

As the electron transporting material, the compound represented by thegeneral formula (1) of the present invention can be used. The layerpreferably contains, as the other materials, aromatic ringtetracarboxylic acid anhydrides, such as pyridine derivatives, quinolinederivatives, pyrimidine derivatives, pyrazine derivatives, phthalazinederivatives, phenanthroline derivatives, triazine derivatives, triazolederivatives, oxazole derivatives, oxadiazole derivatives, imidazolederivatives, fluorenone derivatives, anthraquinodimethane derivatives,anthrone derivatives, diphenylquinone derivatives, thiopyranedioxidederivatives, carbodiimide derivatives, fluorenylidenemethanederivatives, distyrylpyrazine derivatives, naphthalene, and perylene;various metal complexes typified by metal complexes of phthalocyaninederivatives or 8-quinolinol derivatives and metal complexes having metalphthalocyanine, benzoxazole, or benzothiazole as a ligand thereof,organic silane derivatives typified by silole, and the like.

From the viewpoint of decreasing the driving voltage, the thickness ofeach of the electron injecting layer and the electron transporting layeris preferably 500 nm or less.

The thickness of the electron transporting layer is preferably from 1 nmto 500 nm, more preferably from 5 nm to 200 nm, and still morepreferably from 10 nm to 100 nm. In addition, the thickness of theelectron injecting layer is preferably from 0.1 nm to 200 nm, morepreferably from 0.2 nm to 100 nm, and still more preferably from 0.5 nmto 50 nm.

The electron injecting layer and the electron transporting layer mayhave either a single layer structure composed of one kind or two or morekinds of the above-described materials or a multilayer structurecomposed of a plurality of layers having the same composition ordifferent compositions.

The electron injecting layer preferably contains an electron donatingdopant. By incorporating the electron donating dopant in the electroninjecting layer, there are effects that, for example, the electroninjecting properties are improved, the driving voltage is lowered, andthe efficiency is improved. The electron donating dopant may be any oneof organic materials and inorganic materials as long as it is capable ofgiving electrons to the material to be doped and generating radicalanions, and examples thereof include dihydroimidazole compounds such astetrathiafulvalene (TTF), tetrathianaphthacene (TTT), andbis-[1,3-diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, andcesium.

The electron donating dopant in the electron injecting layer iscontained in the amount of preferably from 0.01% by mass to 50% by mass,more preferably from 0.1% by mass to 40% by mass, and still morepreferably 0.5% by mass to 30% by mass, with respect to the total massof the compounds forming the electron injecting layer.

(Hole Blocking Layer)

The hole blocking layer is a layer having a function of preventingholes, which have been transported from the anode side to the lightemitting layer, from passing through to the cathode side. In the presentinvention, the hole blocking layer can be provided as an organic layeradjacent to the light emitting layer on the cathode side.

In order that the T₁ energy of the organic compound in the film stateconstituting the hole blocking layer prevents the energy movement ofexcitons produced in the light emitting layer, and thus, does not lowerthe luminous efficiency, it is preferably higher than the T₁ energy ofthe light emitting material.

Examples of the organic compounds constituting the hole blocking layerinclude aluminum complexes such as aluminum (III)bis(2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as Balq),triazole derivatives, and phenanthroline derivatives such as2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP).

The thickness of the hole blocking layer is preferably from 1 nm to 500nm, more preferably from 5 nm to 200 nm, and still more preferably from10 nm to 100 nm.

The hole blocking layer may have either a single layer structurecomposed of one kind or two or more kinds of the above-describedmaterials or a multilayer structure composed of a plurality of layershaving the same composition or different compositions.

(Electron Blocking Layer)

The electron blocking layer is a layer having a function of preventingthe electrons, which have been transported from the cathode side to thelight emitting layer, from passing through to the anode side. In thepresent invention, the electron blocking layer can be provided as anorganic layer adjacent to the light emitting layer on the anode side.

In order that the T₁ energy of the organic compound in the film stateconstituting the electron blocking layer prevents the energy movement ofexcitons produced in the light emitting layer, and thus, does not lowerthe luminous efficiency, it is preferably higher than the T₁ energy ofthe light emitting material.

As the organic compound constituting the electron blocking layer, forexample, those exemplified above as the hole transporting material canbe used.

The thickness of the electron blocking layer is preferably from 1 nm to500 nm, more preferably from 5 nm to 200 nm, and still more preferablyfrom 10 nm to 100 nm.

The electron blocking layer may have either a single layer structurecomposed of one kind or two or more kinds of from the above-describedmaterials or a multilayer structure composed of a plurality of layershaving the same composition or different compositions.

[Compound Represented by General Formula (HT-1)]

In the organic electroluminescent element of the present invention, itis preferable that the pair of electrodes include an anode, and at leastone organic layer be included between the light emitting layer and theanode, and it is also preferable that the organic layer contains atleast one kind of a compound represented by the following generalformula (HT-1). The triarylamine compound represented by the followinggeneral formula (HT-1) is preferably used as a hole transportingmaterial.

General formula (HT-1)

In the general formula (HT-1), R^(H1) to R^(H15) each independentlyrepresent a hydrogen atom or a substituent.

In the case where R^(H1) to R^(H15) each represent a substituent,examples of the substituent include the substituents selected from theSubstituent Group A, among which an alkyl group, an aryl group, an aminogroup, or a heteroaryl group is preferred, and an alkyl group, an arylgroup, or an arylamino group is more preferred. The substituent may befurther substituted, and the specific examples and the preferred rangeof the additional substituent are the same as in the case where R^(H1)to R^(H15) each represent a substituent.

At least two adjacent groups out of R^(H1) to R^(H15) may form a ringvia a single bond or a linking group. Preferred examples of the linkinggroup include an oxygen atom, a sulfur atom, and an alkylene group.

From the viewpoint of heat resistance and durability, it is preferablethat at least one of R^(H1) to R^(H5) and at least one of R^(H6) toR^(H10) be each an aryl group. Specific examples of the compoundrepresented by the general formula (HT-1) are shown below, but are notlimited thereto.

[Compound Represented by General Formula (O-1)]

The light emitting element of the present invention preferably includesat least one organic layer between the light emitting layer and thecathode, and the organic layer preferably contains at least one ofcompounds represented by the following general formula (O-1), from theviewpoint of the efficiency or driving voltage of an element.Hereinbelow, the general formula (O-1) will be described.

In the general formula (O-1), R^(O1) represents an alkyl group, an arylgroup, or a heteroaryl group. A^(O1) to A^(O4) each independentlyrepresent C—R^(A) or a nitrogen atom. R^(A) represents a hydrogen atom,an alkyl group, an aryl group, or a heteroaryl group, and a plurality ofR^(A)'s may be the same as or different from each other. L^(O1)represents any of divalent to hexavalent linking groups with an arylring or a heteroaryl ring. n^(O1) represents an integer of 2 to 6.

R^(O1) represents an alkyl group (preferably having 1 to 8 carbonatoms), an aryl group (preferably having 6 to 30 carbon atoms), or aheteroaryl group (preferably having 4 to 12 carbon atoms), which mayhave a substituent selected from the above-described Substituent GroupA. R^(O1) is preferably an aryl group or a heteroaryl group, and morepreferably an aryl group. In the case where the aryl group of R^(O1) hasa substituent, examples of the substituent preferably include an alkylgroup, an aryl group, and a cyano group, more preferably an alkyl groupand an aryl group, and still more preferably an aryl group.

In the case where the aryl group of R^(O1) has a plurality ofsubstituents, the plurality of substituents may be bonded to each otherto form a 5- or 6-membered ring. The aryl group of R^(O1) is preferablya phenyl group which may have a substituent selected from SubstituentGroup A, more preferably a phenyl group which may be substituted with analkyl group or an aryl group, and still more preferably an unsubstitutedphenyl group or 2-phenylphenyl group.

A^(O1) to A^(O4) each independently represent C—R^(A) or a nitrogenatom. It is preferable that 0 to 2 groups out of A^(O1) to A^(O4) benitrogen atoms; and it is more preferable that 0 or 1 group out ofA^(O1) to A^(O4) be nitrogen atoms. It is preferable that all of A^(O1)to A^(O4) be C—R^(A), or A^(O1) be a nitrogen atom, and A^(O2) to A^(O4)be C—R^(A); it is more preferable that A^(O1) be a nitrogen atom, andA^(O2) to A^(O4) be C—R^(A); and it is still more preferable that A^(O1)be a nitrogen atom, A^(O2) to A^(O4) be C—R^(A), and R^(A)'s be allhydrogen atoms.

R^(A) represents a hydrogen atom, an alkyl group (preferably having 1 to8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms),or a heteroaryl group (preferably having 4 to 12 carbon atoms), and mayhave a substituent selected from the above-described Substituent GroupA. Further, a plurality of R^(A)'s may be the same as or different fromeach other. R^(A) is preferably a hydrogen atom or an alkyl group, andmore preferably a hydrogen atom.

L^(O1) represents any of a divalent to hexavalent linking group with anaryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring(preferably having 4 to 12 carbon atoms). L^(O1) is preferably anarylene group, a heteroarylene group, an aryltriyl group, or aheteroaryltriyl group, more preferably a phenylene group, a biphenylenegroup, or a benzenetriyl group, and still more preferably a biphenylenegroup or a benzenetriyl group. L^(O1) may have a substituent selectedfrom the above-described Substituent Group A, and in a case of havingthe substituent, the substituent is preferably an alkyl group, an arylgroup, or a cyano group. Specific examples of L^(O1) include thefollowing.

n^(O1) represents an integer of 2 to 6, preferably an integer of 2 to 4,and more preferably 2 or 3. n^(O1) is most preferably 3 from theviewpoint of the efficiency of an element, or most preferably 2 from theviewpoint of the durability of an element.

The compound represented by the general formula (O-1) is more preferablya compound represented by the following general formula (O-2).

In the general formula (O-2), R^(O1) represents an alkyl group, an arylgroup, or a heteroaryl group. R^(O2) to R^(O4) each independentlyrepresent a hydrogen atom, an alkyl group, an aryl group, or aheteroaryl group. A^(O1) to A^(O4) each independently represent C—R^(A)or a nitrogen atom. R^(A) represents a hydrogen atom, an alkyl group, anaryl group, or a heteroaryl group, and a plurality of R^(O1)'s, A^(O1)'sto A^(O4)'s, and R^(O1)'s may be the same as or different from eachother.

R^(O1) and A^(O1) to A^(O4) have the same meaning as R^(O1) and A^(O1)to A^(O4) in the general formula (O-1), and their preferred ranges arealso the same.

R^(O2) to R^(O4) each independently represent a hydrogen atom, an alkylgroup (preferably having 1 to 8 carbon atoms), an aryl group (preferablyhaving 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4to 12 carbon atoms), and these may have a substituent selected from theSubstituent Group A as described above. R^(O2) to R^(O4) are preferablyeach a hydrogen atom, an alkyl group, or an aryl group, more preferablya hydrogen atom or an aryl group, and most preferably a hydrogen atom.

The glass transition temperature (Tg) of the compound represented by thegeneral formula (O-1) is preferably from 100° C. to 300° C., morepreferably from 120° C. to 300° C., still more preferably from 120° C.to 300° C., and even still more preferably from 140° C. to 300° C., fromthe viewpoint of stability at the time of storage at a high temperature,or stable operation during driving at a high temperature or against heatgeneration during driving.

Specific examples of the compound represented by the general formula(O-1) are shown below, but are not limited thereto. In the followingstructural formulae, Ph represents a phenyl group.

The compound represented by the general formula (O-1) can be synthesizedby the method described in JP-A-2001-335776. After the synthesis,purification is preferably carried out by column chromatography,recrystallization, reprecipitation, or the like, and then by sublimationpurification. By the sublimation purification, organic impurities can beseparated and inorganic salts, residual solvents, moisture, or the likecan be removed effectively.

In the light emitting element of the present invention, the compoundrepresented by the general formula (O-1) is preferably included in theorganic layer between the light emitting layer and the cathode, however,it is more preferably included in the layer on the cathode side adjacentto the light emitting layer.

The compound represented by the general formula (O-1) is preferablycontained in the amount of 70% by mass to 100% by mass, and morepreferably 85% by mass to 100% by mass, with respect to the total massof the organic layer added.

(Protective Layer)

In the present invention, the entirety of the organic EL element may beprotected by a protective layer.

For the protective layer, the detailed description in paragraph Nos.[0169] to [0170] of JP-A-2008-270736 can also be applied to the presentinvention.

(Sealing Enclosure)

For the element according to the present invention, the entirety of theelement may be sealed using a sealing enclosure.

For the sealing enclosure, the detailed description in paragraph No.[0171] of JP-A-2008-270736 can be applied to the present invention.

(Driving)

The organic electroluminescent element of the present invention can emitlight by applying a direct current (it may contain an alternate currentcomponent, if necessary) voltage (typically from 2 volts to 15 volts) ora direct current between the anode and the cathode.

As a driving method of the organic electroluminescent element of thepresent invention, driving methods described in JP-A-2-148687,JP-A-6-301355, JP-A-5-29080, JP-A-7-134558, JP-A-8-234685, andJP-A-8-241047, Japanese Patent No. 2784615, and U.S. Pat. Nos. 5,828,429and 6,023,308 can be applied.

The external quantum efficiency of the organic electroluminescentelement of the present invention is preferably 7% or more, and morepreferably 10% or more. As to the numerical value of the externalquantum efficiency, a maximum value of the external quantum efficiencyobtained when the element is driven at 20° C., or a value of theexternal quantum efficiency in the vicinity of 300 cd/m² to 400 cd/m²obtained when the element is driven at 20° C. can be employed.

The internal quantum efficiency of the organic electroluminescentelement of the present invention is preferably 30% or more, morepreferably 50% or more, and still more preferably 70% or more. Theinternal quantum efficiency of the element is calculated by dividing theexternal quantum efficiency by the light extraction efficiency. Thelight extraction efficiency in usual organic EL elements is about 20%,but by taking into consideration the shape of a substrate, the shape ofan electrode, the thickness of an organic layer, the thickness of aninorganic layer, the refractive index of an organic layer, therefractive index of an inorganic layer, or the like, it is possible toincrease the light extraction efficiency to 20% or more.

<Use of Element of the Present Invention>

The element of the present invention can be suitably used for displayelements, displays, backlights, electrophotography, illumination lightsources, recording light sources, exposure light sources, readout lightsources, signs, billboards, interior decorations, opticalcommunications, and the like, in particular, devices driven in a regionof high-intensity luminescence, such as an illumination device and adisplay device.

(Light Emitting Device)

Next, the light emitting device of the present invention will bedescribed with reference to FIG. 2.

The light emitting device of the present invention is formed by usingthe organic electroluminescent element.

FIG. 2 is a cross-sectional view schematically showing one example ofthe light emitting device of the present invention. The light emittingdevice 20 in FIG. 2 includes a transparent substrate (supportingsubstrate) 2, an organic electroluminescent element 10, a sealingenclosure 16, and the like.

The organic electroluminescent element 10 is formed by laminating ananode (first electrode) 3, an organic layer 11, and a cathode (secondelectrode) 9 in this order on the substrate 2. In addition, a protectivelayer 12 is laminated on the cathode 9, and a sealing enclosure 16 isfurther provided via an adhesive layer 14 on the protective layer 12.Incidentally, a part of each of the electrodes 3 and 9, a diaphragm, aninsulating layer, and the like are omitted.

Here, as the adhesive layer 14, a photocurable adhesive such as an epoxyresin, or a thermosetting adhesive can be used, and for example, athermosetting adhesive sheet may also be used.

The light emitting device of the present invention is not particularlylimited in its use, and it can be used as not only an illuminationdevice but also a display device of a television set, a personalcomputer, a mobile phone, electronic paper, or the like.

(Illumination Device)

Next, the illumination device of the present invention will be describedwith reference to FIG. 3.

FIG. 3 is a cross-sectional view schematically showing one example ofthe illumination device of the present invention. The illuminationdevice 40 of the present invention includes, as shown in FIG. 3, theabove-described organic EL element 10 and a light scattering member 30.More specifically, the illumination device 40 is configured such thatthe substrate 2 of the organic EL element 10 and the light scatteringmember 30 are in contact with each other.

The light scattering member 30 is not particularly limited as long as itcan scatter light, but in FIG. 3, a member obtained by dispersing fineparticles 32 in a transparent substrate 31 is used. Suitable examples ofthe transparent substrate 31 include a glass substrate, and suitableexamples of the fine particles 32 include transparent resin fineparticles. As the glass substrate and the transparent resin fineparticles, a known product can be used for both. In such an illuminationdevice 40, when light emitted from the organic electroluminescentelement 10 is incident on the light incident surface 30A of the lightscattering member 30, the incident light is scattered by the lightscattering member 30 and the scattered light is output as illuminatinglight from the light outputting surface 30B.

EXAMPLES

Hereinbelow, the present invention will be described in more detail withreference to Examples, but the present invention is not limited thereto.

1. Synthesis Example (Compound (1-7))

Synthesis of Compound (1-7A)

15 g of m-bromobenzeneboronic acid 1,8-diaminonaphthalene as aprotective group, 29.6 g of potassium triphosphate, 3.8 g of2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), 75 ml oftetrahydrofuran (THF), and 75 ml of distilled water were put into a500-ml 3-neck flask, and the mixture was stirred, degassed, and thenpurged with nitrogen. Under a nitrogen gas flow, 2.1 g oftris(dibenzylideneacetone) dipalladium (Pd₂(dba)₃) and 13.6 g of4-cyanophenylboronic acid were added thereto, and the mixture was heatedand refluxed in an oil bath at 80° C. for 5 hours. After returning toroom temperature, 100 ml of toluene was added thereto, THF wasevaporated under reduced pressure, and then the aqueous layer wasremoved. The organic layer was purified by column chromatography using atoluene/hexane eluent to obtain 9 g of a compound (1-7A).

Synthesis of Compound (1-7B)

9 g of the compound (1-7A), 90 ml of THF, and 9 ml of hydrochloric acidwere put into a 3-neck flask, and the mixture was stirred at roomtemperature for 5 hours. The obtained precipitate was separated byfiltration and the filtrate was washed with an aqueous hydrochloric acidsolution 2 times. The residue was extracted with ethyl acetate and driedunder reduced pressure to obtain 4.5 g of (1-7B).

Synthesis of Compound (1-7C)

3.2 g of 2-bromopyridine, 12.8 g of potassium triphosphate, 1.66 g ofS-phos, 30 ml of THF, and 30 ml of distilled water were put into a3-neck flask, and the mixture was stirred, degassed, and then purgedwith nitrogen. Under a nitrogen gas flow, 0.9 g of Pd₂ (dba)₃ and 4.5 gof the compound (1-7B) were added thereto, and the mixture was heatedand refluxed in an oil bath at 80° C. for 5 hours. After returning toroom temperature, 100 ml of toluene was added thereto, THF wasevaporated under reduced pressure, and then the aqueous layer wasremoved. The organic layer was purified by column chromatography using atoluene/hexane eluent to obtain 3 g of a compound (1-7C).

Synthesis of Compound (1-7)

1.5 g of the compound (1-7D) and 30 ml of isopropanol were put into a100-ml 3-neck flask. Under a nitrogen gas flow, 0.4 g of the compound(1-7C) was added thereto and the mixture was heated and refluxed in anoil bath at 95° C. for 16 hours. After returning to room temperature,the precipitate was filtered and washed with isopropanol. The filtratewas dissolved in 12 ml of chloroform and the solution was purified bysilica gel column chromatography using a chloroform/hexane eluent. Thesolvent was evaporated, the residue was dissolved in dichloromethane,ethanol was then added thereto, and dichloromethane was evaporated in arotary evaporator. The obtained precipitate was separated by filtration,washed with ethanol, and dried in vacuo to obtain 0.45 g of a yellowsolid. The obtained yellow solid was purified by sublimationpurification. Sublimation purification was carried out using TRS-1manufactured by ULVAC-RIKO, Inc. The pressure was reduced toapproximately 9.85×10⁻³ Pa and adjusted to 8.12×10⁻¹ Pa under an argongas flow, and then the temperature was raised to 300° C. to carry outsublimation purification. The crystals attached to a glass tube werecollected using a spatula to obtain 0.33 g of a compound (1-7). The¹H-NMR data of the synthesized compound (1-7) are shown in FIG. 4.

Synthesis Scheme of Compound (1-5)

Synthesis Scheme of Compound (2-12)

Synthesis Scheme of Compound (3-5)

Synthesis Scheme of Compound (6-8)

Synthesis Scheme of Compound (7-1)

The other compounds can be synthesized according to the following schemein the same manner as for the compound (1-7).

R, R′, R″, and R′″ each independently represent a hydrogen atom or asubstituent.

2. Fabrication and Evaluation of Elements Example 1-1

A 0.5 mm-thick and 2.5 cm square glass substrate (manufactured byGeomatec Co., Ltd., surface resistance: 10Ω/□ (Ω/square)) having an ITOfilm thereon was put in a cleaning container. After ultrasonic cleaningin 2-propanol, the glass substrate was subjected to a UV-ozone treatmentfor 30 minutes. The following organic layers were deposited sequentiallyon this transparent anode (ITO film) by a vacuum deposition method.

First layer (charge generating layer): Compound (A): Film thickness 10nm

Second layer (hole transporting layer): HTL-1: Film thickness 30 nm

Third layer (light emitting layer): H-1 (host compound) and Compound(1-7) (light emitting material) (mass ratio of host compound:lightemitting material=85:15): Film thickness 40 nm

Fourth layer (electron transporting layer): ETL-1: Film thickness 40 nm

1 nm of lithium fluoride and 100 nm of metallic aluminum were depositedin this order thereon to form a cathode.

This laminate was put in a glove box purged with a nitrogen gas withoutbringing it into contact with the atmosphere and then sealed with asealing can made of glass and an ultraviolet ray-curable adhesive(XNR5516HV, manufactured by Nagase-Chiba Ltd.) to obtain an element ofExample 1.

Examples 1-2 to 1-10 and Comparative Examples 1-1 to 1-5

In the same manner as in Example 1-1 except that the compound (1-7) ofthe third layer was replaced by a compound shown in Table 1 below in thefabrication of the element of Example 1-1, elements of Examples 1-2 to1-10 and Comparative Examples 1-1 to 1-5 were fabricated.

These elements were evaluated in terms of efficiency, durability, anddriving voltage by the following methods, and the results are shown inTable 1 below.

(Driving Voltage)

Light was emitted by applying a direct current voltage to each elementto give a luminance of 3500 cd/m². The voltage applied at that time wastaken as an index for evaluation of a driving voltage. A case where thedriving voltage is less than 5.5 V was taken as A, a case where thedriving voltage is 5.5 V or more and less than 7 V was taken as B, acase where the driving voltage is 7 V or more was taken as C, and theresults are shown in Table 1 below.

(External Quantum Efficiency)

Light was emitted by applying a direct current voltage to each of theelements using a source measure unit 2400 manufactured by TOYOCorporation. The luminance was measured using a luminance meter BM-8manufactured by Topcon Corporation. The luminous spectrum and the lightemitting peak wavelength were measured using a spectrum analyzer PMA-11manufactured by Hamamatsu Photonics K. K. Based on these values, theexternal quantum efficiency at a luminance in the vicinity of 3500 cd/m²was calculated by using a luminance conversion method.

A case where the external quantum efficiency is 15% or more was taken asA, a case where the external quantum efficiency is 10% or more and lessthan 15% was taken as B, a case where the external quantum efficiency isless than 10% was taken as C, and the results are shown in Table 1below.

(Durability)

Light was continuously emitted by applying a direct current voltage toeach of the elements to give a luminance of 3500 cd/m² at roomtemperature (20° C.), and the time taken until the luminance became 3395cd/m² was taken as an index for durability. How many times thedurability time is taken until the luminance became 3395 cd/m² is thanthe durability time for the element in which the light emitting materialwas replaced by a comparative compound (E-1) (Comparative Example 1-1)was calculated, and shown in Table 1 below. A indicates 2 times or more,B indicates 1.5 times or more and less than 2 times, C indicates 1.1times or more and less than 1.5 times, D indicates 0.5 times or more andless than 1 time, and E indicates less than 0.5 times.

(Possibility of Sublimation Purification of Light Emitting Material)

Sublimation purification was carried out using TRS-1 manufactured byULVAC-RIKO, Inc. The pressure was reduced to approximately 7.0×10⁻² Pa,and the temperature was raised until the sublimation occurred. Thecrystals attached to a glass tube were collected using a spatula. A casewhere 10% or more of the weight before the sublimation can be collectedwas denoted as “possible” and a case where less than 10% of the weightbefore the sublimation can be collected was denoted as “impossible”. Theresults are shown in Table 1.

Examples 2-1 to 6-7 and Comparative Examples 2-1 to 6-1

In the same manner as for the fabrication of the element of Example 1-1except that the materials of the hole transporting layer, the lightemitting materials, and the host compounds were changed as shown inTables 2 to 6 below, the elements of Examples 2-1 to 6-7 and ComparativeExamples 2-1 to 6-1 were fabricated and evaluated in the same manner asin Example 1-1. Further, as for the durability time, how many times thedurability time was than the bases (1.0), which are Comparative Example2-1 in Table 2, Comparative Example 3-1 in Table 3, Comparative Example4-1 in Table 4, Comparative Example 5-1 in Table 5, and ComparativeExample 6-1 in Table 6, respectively, are shown.

TABLE 1 Possibility of sublimation purification Light of Hole emittinglight External Durability transporting material Host emitting Drivingquantum vs (E-1) layer (third layer) compound material voltageefficiency (times) Example 1-1 HTL-1 (1-7) H-1 Possible B B A Example1-2 HTL-1 (1-3) H-1 Possible B B A Example 1-3 HTL-1 (1-5) H-1 PossibleB B B Example 1-4 HTL-1 (1-6) H-1 Possible B B A Example 1-5 HTL-1 (2-3)H-1 Possible B B B Example 1-6 HTL-1 (2-7) H-1 Possible B B B Example1-7 HTL-1 (2-8) H-1 Possible B B B Example 1-8 HTL-1  (2-12) H-1Possible B B B Example 1-9 HTL-1 (3-5) H-1 Possible B B B Example 1-10HTL-1 (6-8) H-1 Possible B B B Comparative HTL-1 (E-1) H-1 Possible B B1.0 Example 1-1 Comparative HTL-1 (E-2) H-1 Possible B B E Example 1-2Comparative HTL-1 (E-3) H-1 Possible B C E Example 1-3 Comparative HTL-1(E-4) H-1 Possible B C E Example 1-4 Comparative HTL-1 (E-5) H-1Impossible — — — Example 1-5

TABLE 2 Possibility of sublimation purification Light of Durability Holeemitting light External vs transporting material Host emitting Drivingquantum (E-1) layer (third layer) compound material voltage efficiency(times) Example 2-1 HTL-1 (1-7) H-2 Possible B B C Comparative HTL-1(E-1) H-2 Possible B B 1.0 Example 2-1

TABLE 3 Possibility of Light sublimation emitting purification Holematerial of light External Durability transporting (third Host emittingDriving quantum vs (E-1) layer layer) compound material voltageefficiency (times) Example 3-1 HTL-1 (1-7) H-3 Possible B B CComparative HTL-1 (E-1) H-3 Possible B B 1.0 Example 3-1

TABLE 4 Possibility of Light sublimation emitting purification Holematerial of light External Durability transporting (third Host emittingDriving quantum vs (E-1) layer layer) compound material voltageefficiency (times) Example 4-1 HTL-1 (1-7) H-4 Possible A B A Example4-2 HTL-1 (2-3) H-4 Possible A B B Example 4-3 HTL-1 (2-7) H-4 PossibleA B A Example 4-4 HTL-1 (2-8) H-4 Possible A B A Example 4-5 HTL-7 (2-12) H-4 Possible A B A Example 4-6 HTL-7 (3-5) H-4 Possible A B AComparative HTL-1 (E-1) H-4 Possible A B 1.0 Example 4-1

TABLE 5 Possibility of Light sublimation emitting purification Holematerial of light External Durability transporting (third Host emittingDriving quantum vs (E-1) layer layer) compound material voltageefficiency (times) Example 5-1 HTL-1 (1-7) H-5 Possible B B BComparative HTL-1 (E-1) H-5 Possible B B 1.0 Example 5-1

TABLE 6 Possibility of Light sublimation emitting purification Holematerial of light External Durability transporting (third Host emittingDriving quantum vs (E-1) layer layer) compound material voltageefficiency (times) Example 6-1 HTL-1 (1-7) H-6 Possible A B A Example6-2 HTL-7 (2-3) H-6 Possible A B A Example 6-3 HTL-7 (2-7) H-6 PossibleA B A Example 6-4 HTL-7 (2-8) H-6 Possible A B A Example 6-5 HTL-7 (2-12) H-6 Possible A B A Example 6-6 HTL-7 (3-5) H-6 Possible A B AExample 6-7 HTL-7 (7-1) H-6 Possible A B A Comparative HTL-1 (E-1) H-6Possible A B 1.0 Example 6-1

From Tables 1 to 6 above, it was found that an organicelectroluminescent element having excellent efficiency at a low drivingvoltage and excellent durability is obtained by using the compoundrepresented by the general formula (1) of the present invention as alight emitting material.

Further, it was found that the organic electroluminescent element usingthe compound represented by the general formula (1) has improveddurability in the case of using a host material having a cyano group,and can be driven at a lowered voltage as well.

In addition, the light emitting peak wavelength of the organicelectroluminescent elements fabricated in Examples 1-1 to 6-7 was from500 nm to 550 nm. Further, as seen from Table 1, in Comparative Example1-5, it was impossible to deposit the light emitting material, and thus,an element could not be fabricated.

In the cases of a light emitting device, a display device, and anillumination device, it is necessary to emit light at a high luminanceinstantly through a high current intensity at each pixel portion. Inthis regard, the light emitting element of the present invention isdesigned to increase the luminous efficiency in such a case, andaccordingly, it can be advantageously used.

In addition, the element of the present invention has excellentdurability and is thus suitable for a light emitting device, a displaydevice, and an illumination device.

Light Emitting Materials Used in Comparative Examples

INDUSTRIAL APPLICABILITY

According to the present invention, an organic electroluminescentelement having a low driving voltage, excellent efficiency, andexcellent durability can be provided. Further, a light emitting device,a display device, and an illumination device each using the organicelectroluminescent element can be provided.

In addition, according to the present invention, an iridium complex usedfor the preparation of the organic electroluminescent element having alow driving voltage, excellent efficiency, and excellent durability canbe provided.

The present invention is described above in detail and with reference tospecific embodiments, but various changes and modifications will beapparent to persons skilled in the art without departing from the spiritand scope of the present invention.

The present application is based on Japanese Patent Application No.2011-218507 filed on Sep. 30, 2011, the contents of which areincorporated herein by reference.

REFERENCE SIGNS LIST

-   -   2: SUBSTRATE    -   3: ANODE    -   4: HOLE INJECTING LAYER    -   5: HOLE TRANSPORTING LAYER    -   6: LIGHT EMITTING LAYER    -   7: HOLE BLOCKING LAYER    -   8: ELECTRON TRANSPORTING LAYER    -   9: CATHODE    -   10: ORGANIC ELECTROLUMINESCENT ELEMENT (ORGANIC EL ELEMENT)    -   11: ORGANIC LAYER    -   12: PROTECTIVE LAYER    -   14: ADHESIVE LAYER    -   16: SEALING ENCLOSURE    -   20: LIGHT EMITTING DEVICE    -   30: LIGHT SCATTERING MEMBER    -   30A: LIGHT INCIDENT SURFACE    -   30B: LIGHT OUTPUTTING SURFACE    -   31: TRANSPARENT SUBSTRATE    -   32: FINE PARTICLES    -   40: ILLUMINATION DEVICE

1.-13. (canceled)
 14. A compound represented by the following generalformula (1):

wherein R₁₁₁ to R₁₃₄ each independently represent a hydrogen atom or asubstituent; at least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ andR₁₁₅, at least two adjacent groups out of R₁₁₅ to R₁₁₈, at least twoadjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, at least twoadjacent groups out of R₁₂₃ to R₁₂₆, at least two adjacent groups out ofR₁₂₇ to R₁₃₀, R₁₃₀ and R₁₃₁, or at least two adjacent groups out of R₁₃₁to R₁₃₄ may be bonded to each other to form a ring; provided that atleast one of R₁₁₁ to R₁₃₄ represents a group represented by thefollowing general formula (A):

X represents a cyano group or a halogenated alkyl group; L represents asingle bond or a divalent linking group; R represents a substituent,wherein when a plurality of R's are present, they may be the same as ordifferent from each other; n represents an integer of 0 to 4; and *represents a binding site.
 15. The compound of claim 1, wherein thecompound represented by the general formula (1) is a compoundrepresented by the following general formula (2):

wherein R₁₁₁ to R₁₂₃, R₁₂₅, R₁₂₆, and R₂₁₁ to R₂₁₅ each independentlyrepresent a hydrogen atom or a substituent, wherein two groups out ofR₁₁₁ to R₁₁₈ may be each the same as or different from each other; atleast two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, at leasttwo adjacent groups out of R₁₁₅ to R₁₁₈, at least two adjacent groupsout of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, R₁₂₅ and R₁₂₆, or at least twoadjacent groups out of R₂₁₁ to R₂₁₅ may be bonded to each other to forma ring; and L represents a single bond or a divalent linking group;provided that at least one of R₂₁₁ to R₂₁₅ represents a cyano group or ahalogenated alkyl group.
 16. The compound of claim 1, wherein thecompound represented by the general formula (1) is a compoundrepresented by the following general formula (3):

wherein R₁₁₁ to R₁₁₅, R₁₁₇, R₁₁₈, R₁₁₉ to R₁₂₆, and R₃₁₁ to R₃₁₅ eachindependently represent a hydrogen atom or a substituent, wherein twogroups out of R₁₁₁ to R₁₁₅, R₁₁₇, R₁₁₈, and R₃₁₁ to R₃₁₅ may be each thesame as or different from each other; at least two adjacent groups outof R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, R₁₁₇ and R₁₁₈, at least two adjacentgroups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, at least two adjacent groupsout of R₁₂₃ to R₁₂₆, or at least two adjacent groups out of R₃₁₁ to R₃₁₅may be bonded to each other to form a ring; and L represents a singlebond or a divalent linking group; provided that at least one of R₃₁₁ toR₃₁₅ represents a cyano group or a halogenated alkyl group.
 17. Thecompound of claim 1, wherein the compound represented by the generalformula (1) is a compound represented by the following general formula(4):

wherein R₁₁₁ to R₁₂₀, R₁₂₂ to R₁₂₆, and R₄₁₁ to R₄₁₅ each independentlyrepresent a hydrogen atom or a substituent, wherein two groups out ofR₁₁₁ to R₁₁₈ may be each the same as or different from each other; atleast two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, at leasttwo adjacent groups out of R₁₁₅ to R₁₁₈, R₁₁₉ and R₁₂₀, R₁₂₂ and R₁₂₃,at least two adjacent groups out of R₁₂₃ to R₁₂₆, or at least twoadjacent groups out of R₄₁₁ to R₄₁₅ may be bonded to each other to forma ring; and L represents a single bond or a divalent linking group;provided that at least one of R₄₁₁ to R₄₁₅ represents a cyano group or ahalogenated alkyl group.
 18. The compound of claim 1, wherein thecompound represented by the general formula (1) is a compoundrepresented by the following general formula (5)

wherein R₁₁₁, R₁₁₂, R₁₁₄, R₁₁₅ to R₁₂₆, and R₅₁₁ to R₅₁₅ eachindependently represent a hydrogen atom or a substituent, wherein twogroups out of R₁₁₁, R₁₁₂, R₁₁₄, R₁₁₅ to R₁₁₈, and R₅₁₁ to R₅₁₅ may beeach the same as or different from each other; R₁₁₁ and R₁₁₂, R₁₁₄ andR₁₁₅, at least two adjacent groups out of R₁₁₅ to R₁₁₈, at least twoadjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, at least twoadjacent groups out of R₁₂₃ to R₁₂₆, or at least two adjacent groups outof R₅₁₁ to R₅₁₅ may be bonded to each other to form a ring; and Lrepresents a single bond or a divalent linking group; provided that atleast one of R₅₁₁ to R₅₁₅ represents a cyano group or a halogenatedalkyl group.
 19. The compound of claim 1, wherein the compoundrepresented by the general formula (1) is a compound represented by thefollowing general formula (6):

wherein R₁₁₁ to R₁₂₄, R₁₂₆, and R₆₁₁ to R₆₁₅ each independentlyrepresent a hydrogen atom or a substituent, wherein two groups out ofR₁₁₁ to R₁₁₈ may be each the same as or different from each other; atleast two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ and R₁₁₅, at leasttwo adjacent groups out of R₁₁₅ to R₁₁₈, at least two adjacent groupsout of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, R₁₂₃ and R₁₂₄, or at least twoadjacent groups out of R₆₁₁ to R₆₁₅ may be bonded to each other to forma ring; and L represents a single bond or a divalent linking group;provided that at least one of R₆₁₁ to R₆₁₅ represents a cyano group or ahalogenated alkyl group.
 20. The compound of claim 1, wherein X in thegeneral formula (A) is a cyano group.
 21. An organic electroluminescencedevice, comprising: a substrate; Amendment and Response to Notice toFile Missing Parts a pair of electrodes including an anode and acathode, disposed on the substrate; and at least one organic layerincluding a light emitting layer, disposed between the electrodes;wherein at least one compound represented by the following generalformula (1) is contained in at least one of the organic layers:

wherein R₁₁₁ to R₁₃₄ each independently represent a hydrogen atom or asubstituent; at least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ andR₁₁₅, at least two adjacent groups out of R₁₁₅ to R₁₁₈, at least twoadjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, at least twoadjacent groups out of R₁₂₃ to R₁₂₆, at least two adjacent groups out ofR₁₂₇ to R₁₃₀, R₁₃₀ and R₁₃₁, or at least two adjacent groups out of R₁₃₁to R₁₃₄ may be bonded to each other to form a ring; provided that atleast one of R₁₁₁ to R₁₃₄ represents a group represented by thefollowing general formula (A):

X represents a cyano group or a halogenated alkyl group; L represents asingle bond or a divalent linking group; R represents a substituent,wherein when a plurality of R's are present, they may be the same as ordifferent from each other; n represents an integer of 0 to 4; and *represents a binding site.
 22. The organic electroluminescent elementaccording to claim 21, wherein a compound represented the generalformulae (1) is contained in the light emitting layer.
 23. The organicelectroluminescent element according to claim 22, further containing acompound having a cyano group, in addition to the compound representedby the general formulae (1), in the light emitting layer.
 24. A lightemitting device using the organic electroluminescent element accordingto claim
 21. 25. A display device using the organic electroluminescentelement according to claim
 21. 26. An illumination device using theorganic electroluminescent element according to claim
 21. 27. A thinfilm comprising a compound of the general formula (1):

wherein R₁₁₁ to R₁₃₄ each independently represent a hydrogen atom or asubstituent; at least two adjacent groups out of R₁₁₁ to R₁₁₄, R₁₁₄ andR₁₁₅, at least two adjacent groups out of R₁₁₅ to R₁₁₈, at least twoadjacent groups out of R₁₁₉ to R₁₂₂, R₁₂₂ and R₁₂₃, at least twoadjacent groups out of R₁₂₃ to R₁₂₆, at least two adjacent groups out ofR₁₂₇ to R₁₃₀, R₁₃₀ and R₁₃₁, or at least two adjacent groups out of R₁₃₁to R₁₃₄ may be bonded to each other to form a ring, provided that atleast one of R₁₁₁ to R₁₃₄ represents a group represented by thefollowing general formula (A):

X represents a cyano group or a halogenated alkyl group; L represents asingle bond or a divalent linking group; R represents a substituent,wherein when a plurality of R's are present, they may be the same as ordifferent from each other; n represents an integer of 0 to 4; and *represents a binding site.